How to Make Your Boyfriend Happy over Text

Expert tips to cheer up your boyfriend over text messaging

Written by John Keegan | Edited by Amy Bobinger

Last Updated: August 24, 2022 References

While you might want to spend every moment snuggled up next to your boyfriend, there are inevitably going to be times when you have to be apart. Luckily, texting can be a fun way to keep things feeling fresh until the next time you're together. Keeping up a flirty text conversation can be a bit of an art, but we're here with plenty of tips that will have your boyfriend lighting up every time he sees your name on his screen.

This article is based on an interview with our professional dating coach, John Keegan, founder of The Awakened Lifestyle. Check out the full interview here.

1

Send him a pic.

Snap a shot of whatever you have going on. Of course, selfies always work, especially if you're having an especially great hair day or your outfit is amazing. But turn that camera around once in a while, too. Show him things like your neighbor's cute cat, the amazing view from your lunch meeting, or some cool street art you passed on your way to meet a friend.^{[1]
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- Not only will this help spark a conversation, but it will show him the cool, interesting things you have going on—and that's only going to make him want to be around you more!^{[2]
  X
  Expert Source
  
  John Keegan
  Dating Coach
  Expert Interview. 25 May 2021.}

2

Compliment him.

Text him what you really like about him. If you really want to put a smile on your boyfriend's face, surprise him with an out-of-the-blue compliment. Make it feel really personal by choosing something specific that's really unique to him.^{[3]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 5 November 2019.}
- Get flirty with a compliment about his looks, like: "That shirt you were wearing today really showed off your toned arms. I can tell you've been working hard at the gym! You look amazing."
- Get in touch with his softer side by complimenting something about his character. Say something like, "You have this way of always making me feel better when I'm down. You always know the right thing to say!"

3

Tell him when something reminds you of him.

Let him know he's on your mind. Do you ever wonder if your boyfriend is thinking of you when you're not together? Chances are he does the same thing. The next time something makes you think of him, no matter how small, grab your phone and shoot him a quick text!^{[4]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 5 November 2019.}
- If you hear a song that made you think of him, send him a link and a simple text like "aww it's us!"^{[5]
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  Expert Source
  
  Cher Gopman
  Dating Coach
  Expert Interview. 17 May 2019.}
- If you pass a restaurant where the two of you have eaten, send him a pic and a note like, "This was such a fun night! Let's do it again soon."
- Make him laugh by reminding him of an inside joke, like texting him a picture of a frog with a caption like, "OMG it's that singer we heard at the bar that night!"

4

Ask questions to get him to open up about himself.

Use texts to get to know each other better. Giving your boyfriend a chance to talk about himself will help him feel appreciated and cared for. Ask him about his day when you first start talking. Then, sprinkle in questions throughout the conversation to keep things rolling.^{[6]
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Expert Source

Cher Gopman
Dating Coach
Expert Interview. 17 May 2019.} Just don't hit him with non-stop questions or it will start to feel like an interrogation.^{[7]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 5 November 2019.}
- Try asking about his favorite childhood memories, dreams about the future, or even what he wants for lunch—anything that will get him talking about himself.
- Get silly with random questions that will put him on the spot, like, "If you could only ever listen to one band again, who would it be?" or "Pineapple on pizza, yes or no?"

5

Ask him for a recommendation.

Let him know you value his opinion. When you ask your boyfriend to help you decide something, it's a subtle way to show him that you think he has good taste. Is there anything more flattering than that? Just make sure you're willing to go with whatever he chooses. He might get offended if you ask his opinion and then do the opposite!^{[8]
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- For instance, you might send him a picture of two shirts and ask which one he thinks you should wear.
- Looking for something new to listen to? Ask him to recommend one of his favorite albums!

6

Open with something interesting.

Skip boring intros like "hey" or "wyd?" Greetings like that can make him feel like you just decided to text him because you're sitting around with nothing going on. Instead, jump right in with something that feels spontaneous and fun—like you texted him because you just couldn't wait to tell him something!^{[9]
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Expert Source

Joshua Pompey
Relationship Expert
Expert Interview. 4 December 2019.}
- Try drawing him in with a hook that will build anticipation, like, "You're never going to believe who I just saw!" or "Guess what happened in math today!"
- You could also link back to a conversation you had earlier by saying something like, "You know how we were just talking about Greek food the other day? I found this awesome place we should try this weekend."

7

Tell him something about your day.

Make him feel like he's there with you. It doesn't necessarily have to be ground-breaking. Just try to think of something that you can share that will make him feel like he's a part of your life. Once the conversation is going, you can shift to something flirty to keep him on his toes.^{[10]
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Expert Source

Joshua Pompey
Relationship Expert
Expert Interview. 4 December 2019.}
- For instance, you might text him something like, "My new coworker has a super annoying habit," or, "I watched a cool movie today that I think you'd like."

8

Laugh when he makes a joke.

Even a simple "lol" or laugh emoji can make him smile. Everybody likes to feel like they're appreciated, so if your boyfriend cracks a joke, take a moment to let him know you think he's the funniest guy around. It's not that hard to let him know you're laughing—try something like "lol lol," "omg!" or a string of laughing emojis.^{[11]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 25 May 2021.}
- Laughing at somebody's jokes is an age-old way to flirt. You're just bringing it into the digital age!

9

Talk to him about something that you're interested in.

Let him get a glimpse into your world. Don't feel like you have to spend your whole text conversation talking about him. If you have something going on that you think is really cool or you know a lot about, bring it up! When you share something you're passionate about, that enthusiasm is usually contagious, so let him know why you think it's super cool.^{[12]
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Expert Source

Cher Gopman
Dating Coach
Expert Interview. 17 May 2019.}
- For example, if you're really into paleontology and you come across a news article about a new dinosaur species, send it to him! If he doesn't know a lot about it, give him a little context, like, "This is the first time they've found a new fossil in this area in over 50 years!"

10

Tease him a little.

Get playful, but not mean. Most guys will recognize that a little light teasing means you like them, but be careful with this one. Don't make jokes about anything he might be really sensitive about. Keep it really lighthearted and positive—you want it to come across as flirtatious, after all.^{[13]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 25 May 2021.}
- One of the best ways to tease someone is to focus on something that's actually one of their strengths. If your boyfriend is an awesome basketball player, for instance, you might say, "Hey tomorrow let's meet at the gym and I'll show you how to shoot a 3-pointer!"

11

Share fun date ideas.

Give him ideas of things you could do together. Get him excited about seeing you again by letting him know where you'd like to go and what you'd like to do next. Not only does that take some of the pressure off him to constantly come up with creative date ideas, but it also gives him insight into the type of stuff you're into. Even better, it lets him know that you're looking forward to seeing him again soon.^{[14]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 25 May 2021.}
- If you hear about a band playing in town, you might send him a link to the event and say something like, "I was thinking of buying tickets to this. Wanna go?"

12

Be there for him when he has a bad day.

Don't try to fix everything; just listen. Everybody has a tough day sometimes. If you know your sweetheart had a bad day at work, if he's not feeling well, or if he's dealing with something stressful, do your best to let him know you care. Listen to him if he wants to talk about it, but don't push him if he doesn't. Either way, let him know you're there, and ask if there's anything you could do that would make him feel better.^{[15]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 5 November 2019.}
- Don't follow up with a bunch of suggestions about what he should do unless he specifically asks for your advice. Sometimes people just need to vent to a supportive listener.^{[16]
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  Expert Source
  
  Cher Gopman
  Dating Coach
  Expert Interview. 17 May 2019.}

13

Get a little flirty.

Turn up the heat if you're both comfortable with that. Flirting with your boyfriend through text doesn't always have to be tame. If you have something steamy on your mind, start by hinting around at it to see if he's receptive. Something like a flirty emoji or a song with sexy lyrics can be a great way to ease the conversation in more of an intimate direction. You could also just tell him what you're thinking about by saying something like, "You've been on my mind all day. Last night was amazing!"^{[17]
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Expert Source

John Keegan
Dating Coach
Expert Interview. 5 November 2019.}
- Some people don't like to get too racy in their texts, so if either one of you aren't crazy about the idea of dirty talk or suggestive photos, that's totally fine. You can always flirt in person if you prefer!^{[18]
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